Hawaiian Island Cruises

1 Cruise
4 Offers
See the Hawaiian Islands as few do—from the outside in, sailing from island to island on a small ship cruise. Hike remote shorelines and snorkel at sea as you cruise Molokai, Lanai, Maui and Hawaii.
Trips, Tours & Cruises

Hawaii Island Hopping by Small Ship

Get Aboard
1 Cruise
4 Offers

With tens of millions visiting the Aloha state each year, take a Hawaii island hopping cruise for an entirely new, off-the-beaten-path travel experience. Maybe you have been to Hawaii before, but never like this. While day cruises are common, overnight Hawaiian Island cruises are few and far between. Staying aboard a small ship offers unique opportunities to travel in an efficient and effortless way while never missing a sunset. Leave airport travel and hotel bag-packing behind to go Hawaii island hopping in style and ease.

Our Hawaiian Island cruises reach ports and locations that are off-the-beaten path and away from the typical Hawaii cruise destinations. These relaxed, intimate and active Hawaii small ship cruises may just offer the new spin on Aloha luxury you’ve been searching for. Your itinerary is flexible and not available to larger ships, making this Hawaii interisland cruise experience uncrowded, unrushed and full of active adventure exploring remote locales by foot, kayak, sailboat, paddleboard and motor launch.

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Hawaii Small Ship Cruises
with AdventureSmith

We offer the most unique, intimate way to visit Hawaii—by yacht. Let us take you there with efficiency and ease. Why book your Hawaii interisland cruise with AdventureSmith Explorations?

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Work with one Adventure Specialist to prepare for your Hawaii island hopping cruise.

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We can match you with the best Hawaiian cruise & timing thanks to our years of experience.

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Snorkel, whale watch, hike, kayak & paddleboard all in one trip, included in the cost.

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We’re here to help you save with our partnerships & exclusive Hawaii cruise deals.

Three yellow kayaks paddle off the coast of Maui on a Hawaiian Islands cruise

Hawaii Cruises 2024 & 2025

Small ship Hawaii cruises in 2024 are hotter than ever thanks to travelers seeking more exclusivity and remoteness for their travels. Be among the few to cruise Hawaii. Our specialists make it easier than ever to go Hawaii island hopping. Skip the crowds and logistics of air travel and island hop Hawaii by small ship cruise. Our team can assist you with your trip this year, or Hawaii cruises in 2025 and beyond. 

Luxury Hawaii Cruises & Private Yacht Charters

Through AdventureSmith and our expertise with small ship cruising worldwide, you have the power to choose from scheduled Hawaii small ship cruises in Hawaii or design your own Hawaii island hopping charter cruise for an even more intimate experience with your small group. Let our award-winning experts skilled in pairing travelers with the right ship at the best price create the perfect Hawaii boat cruise for you. Think fresh-caught fish and tropical shorelines just for your group! Luxury Hawaii cruises are hard to find with mostly big ships and day cruises dominating the waters. Let us steer you to the best Hawaiian Island cruises that tap into authentic Aloha.

Seared ono fish on a plate with white wine and a Hawaiian Island shirt in the background

Cruising Hawaii offers a way to reach many of the islands, letting the captain and a flexible itinerary be your guide.


Hawaiian Island Cruises

Temperature & Rainfall

Month Jan Feb Mar Apr May Jun Jul Aug Sep Oct Nov Dec
Avg. High (F) 80 80 82 82 84 86 88 88 88 86 84 81
Avg. Low (F) 66 66 67 69 70 72 74 74 74 73 70 67
Avg. Water Temp (F) 76 76 76 76 76 76 80 80 80 80 80 80
Avg. Rainfall (Inches) 3.3 2.4 2.7 1.3 1.0 0.4 0.6 0.6 0.7 2.0 2.8 3.4

Year-Round Hawaii Island Hopping

In Hawaii, winter is warm and summer is warmer. Even in “winter,” temperatures are regularly in the 80s, making it an incredible destination for year-round Hawaiian Island cruises. While rain is common, your small ship captain can navigate to windward and leeward sides of islands to take advantage of unique microclimates and steer you away from rain storms. Taking a Hawaii island hopping cruise can truly ensure you land in the best weather during your vacation.

Want to Learn More About Hawaii’s Climate?

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As I drift off to sleep I begin to dream of the amazing experiences that I couldn't even have imagined only seven days ago. I dream of diving with manta rays, of Pele, the goddess of fire, of paddle boarding at Shark's Fin Cove and swimming in the cool water under the cascading falls of Moâ'oula.
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Book with the confidence that comes from experience.

100+ combined years of experience, 7 continents explored, decades of expedition cruising around the world & here to help you find & book your dream trip.

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